Explore the Best Summer Destinations for 2026

School is finally out, the days are delightfully long, and the highly anticipated summer break has officially arrived. It is time to trade your everyday routine for new adventures, whether you are planning an epic European getaway, a quick city escape, or a relaxing week on the beach. 

However, getting to YYZ should not be the hardest part of your trip. Bumper-to-bumper traffic on the highway, steep long-term parking fees, and unpredictable ride-share prices can easily start your vacation off on the wrong foot. 

UP Express has you covered with a smooth, stress-free departure. In just 28 minutes, you can travel from downtown Toronto’s Union Station straight to YYZ. With spacious trains running every 15 minutes, you can skip the highway gridlock entirely, save your money for vacation experiences rather than parking costs, and dodge surge pricing. Starting your summer holiday with a fast, reliable ride means you arrive at the airport relaxed and ready for takeoff. Travelling with family or friends? Groups of 3-5 can save up to 36% on one-way fares with the UP Group Pass.

When is Summer Break in Canada?

Across most of Canada, summer break kicks off in late June and stretches into early September. This gives families, students, and educators a solid two-month window to explore the world. Naturally, July and August stand as the undisputed peak travel months across the country. During this time, airports, hotels, and popular tourist spots see their highest volume of visitors. 

Summer 2026 is shaping up to be exceptionally busy for travel in and out of Toronto. With major international sporting events, street festivals, and celebrations taking place across the city from June through September, both Toronto Pearson Airport and downtown Toronto are expected to welcome more domestic and international visitors. Whether you're arriving in the city or heading off on your own summer adventure, planning ahead will help make your journey smoother. 

If you're travelling through Toronto Pearson Airport this summer, be sure to book flights, accommodations, and airport transportation as early as possible. Securing your plans in advance can help you access better rates and avoid last-minute stress. For a reliable connection between YYZ and downtown Toronto, take UP Express, with frequent departures and a convenient 28-minute journey. 

Best Travel Destinations in Summer

Finding the perfect summer destination depends entirely on what kind of experience you want. Whether you crave historic architecture, bustling city energy, or kid-friendly entertainment, 2026 offers incredible travel destination options. 

European Escapes

Italy 

Summer in Italy is a dream built on incredible food, rich history, and stunning coastlines. You can spend your days wandering the ancient streets of Rome, marvelling at the Colosseum before stopping for a scoop of authentic gelato. If you prefer the water, head south to the Amalfi Coast. Here, colourful cliffside villages meet the sparkling Mediterranean Sea. Take a boat tour, eat fresh seafood pasta, and soak in the brilliant sunshine. 

Portugal 

Portugal remains one of the most exciting European destinations for Canadian travellers. Start your journey in Lisbon, where vintage yellow trams navigate steep, winding streets. The city offers incredible bakeries, historic castles, and vibrant nightlife. For a slower pace, take a train down to the Algarve region. The southern coast boasts dramatic limestone cliffs, hidden caves, and some of the best surfing beaches in Europe. 

Scotland

If you want to escape the extreme summer heat, Scotland provides a cool, lush, and culturally rich alternative. Explore the historic Royal Mile in Edinburgh, a city dominated by a magnificent hilltop castle. From there, rent a car and drive into the Scottish Highlands. You will discover deep lochs, rugged mountains, and ancient ruins shrouded in mist. It is an ideal destination for hikers and nature lovers looking for dramatic landscapes. 

U.S. City Trips

New York City 

There is never a bad time to visit New York City, but summer brings a special kind of magic to the streets. Central Park comes alive with outdoor concerts, picnicking families, and bike riders. You can catch a spectacular Broadway show, walk the elevated High Line park, or grab a slice of famous New York pizza in Brooklyn. With countless museums and endless shopping, NYC offers a fast-paced weekend getaway just a short flight from Toronto. 

Chicago 

Often called the architectural capital of the United States, Chicago shines in the summer months. Take a boat tour down the Chicago River to learn about the towering skyscrapers that define the city skyline. Spend an afternoon relaxing on the sandy shores of Lake Michigan, which feels more like an ocean than a lake. Do not leave without trying a hearty slice of deep-dish pizza and catching a baseball game at the historic Wrigley Field. 

Family-Friendly Options

Orlando 

For families with children, Orlando remains the ultimate vacation headquarters. It is home to the world’s most famous theme parks, offering endless entertainment for kids and adults alike. From magical castles and thrilling roller coasters to expansive water parks, you can easily fill a week with non-stop action. Many resorts cater specifically to families, featuring massive pools, kids' clubs, and easy transportation to the parks. 

London 

Taking kids across the pond to London is an unforgettable experience. The city is packed with history that feels like it was pulled straight from a storybook. Watch the changing of the guard at Buckingham Palace, ride the massive London Eye Ferris wheel, and explore the interactive exhibits at the Natural History Museum. For fans of magic, the Harry Potter studio tours just outside the city offer a behind-the-scenes look at the beloved film series. 

Honolulu 

For a truly tropical family vacation, Honolulu blends natural beauty with welcoming Hawaiian culture. Waikiki Beach offers gentle waves perfect for young swimmers and beginner surfers. Families can hike up the iconic Diamond Head crater for panoramic views of the island. Beyond the beach, you can attend a traditional luau, learn about marine life at the local aquarium, and enjoy incredible fresh fruit and seafood. 

Summer Travel Within Canada

You do not need your passport to have an incredible summer vacation. Canada offers some of the most diverse and stunning landscapes on the planet, stretching from the Pacific Ocean to the Atlantic coast.

Vancouver 

Nestled between the ocean and the mountains, Vancouver is a playground for outdoor enthusiasts. You can spend the morning biking around the massive Stanley Park seawall and the afternoon hiking up Grouse Mountain. The city boasts a thriving culinary scene, featuring incredible Asian cuisine and fresh Pacific seafood. 

Tofino 

Located on the rugged west coast of Vancouver Island, Tofino is Canada’s surf capital. Even in the summer, the area maintains a moody, beautiful atmosphere with ancient rainforests right on the edge of the beach. You can take whale-watching tours, look for black bears along the shoreline, or simply enjoy a quiet fire on the beach as the sun goes down. 

Banff and Calgary 

A trip to Alberta offers a perfect mix of city energy and wild nature. Start in Calgary, a dynamic city known for its excellent restaurants and massive summer festivals. From there, drive just an hour and a half into the Rocky Mountains to reach Banff. The vibrant turquoise waters of Lake Louise and Moraine Lake look completely surreal. You can hike mountain trails, soak in natural hot springs, and spot elk wandering near the town centre. 

Montreal 

If you want a taste of European charm without crossing the Atlantic, Montreal is just a quick flight from Toronto Pearson. Walk the cobblestone streets of Old Montreal, admire the historic architecture, and stop at a local cafe for fresh pastries. The city is famous for its massive summer music and comedy festivals, bringing incredible energy to the streets day and night. 

Prince Edward Island  PEI is the perfect destination for a slower, more relaxing vacation. The island is famous for its distinctive red sand beaches, rolling green hills, and warm coastal waters. Fans of literature can visit the Green Gables Heritage Place, while food lovers can enjoy some of the best oysters and potatoes in the country. Rent a bicycle and ride the Confederation Trail, which spans the entire province. 

Bay of Fundy, New Brunswick  Nature lovers must visit the Bay of Fundy to witness the highest tides in the world. Twice a day, massive volumes of water rush in and out of the bay, dramatically changing the landscape. You can walk on the ocean floor at Hopewell Rocks during low tide, and then return a few hours later to kayak around those exact same rock formations. 

Cheap Summer Travel

Summer travel does not have to drain your bank account. With a few strategic choices, you can plan a memorable vacation while keeping your budget intact. 

First, consider the days you fly. Travelling mid-week, specifically on Tuesdays and Wednesdays, is almost always cheaper than flying on a Friday or Sunday. Airlines price their tickets based on demand, and weekends are highly sought after by most travellers. 

Second, book your flights and accommodations as early as possible. As planes and hotels fill up, prices naturally rise. Waiting for a last-minute deal in July or August is risky and rarely pays off. 

Third, pack light. Most airlines now charge significant fees for checked luggage. By fitting your summer wardrobe into a carry-on bag, you can save a substantial amount of money for every person in your group. Plus, you will save time at the airport by skipping the baggage claim carousel. 

Finally, consider shifting your travel dates. If you travel in early June or late August, you can often find much better value. During these shoulder weeks, many families are still dealing with school, meaning demand dips slightly, bringing prices down with it. 

If you are looking for budget-friendly destination options, look south. While the Caribbean and Mexico are wildly popular in the winter, they offer incredible off-season deals during the summer months. 

Cancun 

Resorts in Cancun drop their prices significantly in the summer. You can score a massive discount on a luxury all-inclusive package, giving you unlimited food, drinks, and pool access for a fraction of the winter cost. 

Mexico City 

For a cultural trip that is gentle on the wallet, Mexico City is incredible. The food scene is world-class and extremely affordable, from street tacos to high-end dining. You can explore massive historic city squares, ancient ruins just outside the city, and beautiful urban parks without spending a fortune. 

Dominican Republic 

Similar to Cancun, the Dominican Republic offers excellent off-season rates. Destinations like Punta Cana feature pristine white-sand beaches and family-friendly resorts that aggressively discount their rooms during the summer. 

Start Your Vacation the Right Way

Planning a spectacular summer vacation requires time and effort, but getting to the airport should be effortless. No matter where 2026 takes you—from the rugged Scottish Highlands to the red sands of Prince Edward Island—taking UP Express to and from Toronto Pearson Airport is a smart, affordable part of your journey. 

Rely on our fast and reliable service to bypass the stress of city traffic and soaring parking fees. Let UP Express handle the drive so you can sit back, relax, and start focusing on the incredible summer break ahead. Get your tickets online today and get ready to explore the world!